Pavlović, Vladimir D.

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907e875f-3d06-4b95-a065-6978a1613cfb
  • Pavlović, Vladimir D. (8)

Author's Bibliography

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2850
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J.. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules
Elsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .
Jeremić, Sanja, Đokić, Lidija, Ajdačić, Vladimir, Božinović, Nina S., Pavlović, Vladimir D., Manojlović, Dragan D., Babu, Ramesh P., Senthamaraikannan, Ramsankar, Rojas, Orlando, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .
14
14
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Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2866
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J.. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules
Elsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .
Jeremić, Sanja, Đokić, Lidija, Ajdačić, Vladimir, Božinović, Nina S., Pavlović, Vladimir D., Manojlović, Dragan D., Babu, Ramesh P., Senthamaraikannan, Ramsankar, Rojas, Orlando, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .
14
14
14

Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001

Kekez, Branka; Gojgić-Cvijović, Gordana D.; Jakovljević, Dragica M.; Pavlović, Vladimir D.; Beškoski, Vladimir; Popović, Aleksandar R.; Vrvić, Miroslav M.; Nikolić, Vladimir

(Elsevier Sci Ltd, Oxford, 2016)

TY  - DATA
AU  - Kekez, Branka
AU  - Gojgić-Cvijović, Gordana D.
AU  - Jakovljević, Dragica M.
AU  - Pavlović, Vladimir D.
AU  - Beškoski, Vladimir
AU  - Popović, Aleksandar R.
AU  - Vrvić, Miroslav M.
AU  - Nikolić, Vladimir
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3624
PB  - Elsevier Sci Ltd, Oxford
T2  - Carbohydrate Polymers
T1  - Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001
ER  - 
@misc{
author = "Kekez, Branka and Gojgić-Cvijović, Gordana D. and Jakovljević, Dragica M. and Pavlović, Vladimir D. and Beškoski, Vladimir and Popović, Aleksandar R. and Vrvić, Miroslav M. and Nikolić, Vladimir",
year = "2016",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Carbohydrate Polymers",
title = "Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001"
}
Kekez, B., Gojgić-Cvijović, G. D., Jakovljević, D. M., Pavlović, V. D., Beškoski, V., Popović, A. R., Vrvić, M. M.,& Nikolić, V.. (2016). Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001. in Carbohydrate Polymers
Elsevier Sci Ltd, Oxford..
Kekez B, Gojgić-Cvijović GD, Jakovljević DM, Pavlović VD, Beškoski V, Popović AR, Vrvić MM, Nikolić V. Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001. in Carbohydrate Polymers. 2016;..
Kekez, Branka, Gojgić-Cvijović, Gordana D., Jakovljević, Dragica M., Pavlović, Vladimir D., Beškoski, Vladimir, Popović, Aleksandar R., Vrvić, Miroslav M., Nikolić, Vladimir, "Supplementary data for the article: Kekez, B.; Gojgić-Cvijović, G.; Jakovljević, D.; Pavlović, V.; Beškoski, V.; Popović, A.; Vrvić, M. M.; Nikolić, V. Synthesis and Characterization of a New Type of Levan-Graft-Polystyrene Copolymer. Carbohydrate Polymers 2016, 154, 20–29. https://doi.org/10.1016/j.carbpol.2016.08.001" in Carbohydrate Polymers (2016).

Synthesis and characterization of a new type of levan-graft-polystyrene copolymer

Kekez, Branka; Gojgić-Cvijović, Gordana D.; Jakovljević, Dragica M.; Pavlović, Vladimir D.; Beškoski, Vladimir; Popović, Aleksandar R.; Vrvić, Miroslav M.; Nikolić, Vladimir

(Elsevier Sci Ltd, Oxford, 2016)

TY  - JOUR
AU  - Kekez, Branka
AU  - Gojgić-Cvijović, Gordana D.
AU  - Jakovljević, Dragica M.
AU  - Pavlović, Vladimir D.
AU  - Beškoski, Vladimir
AU  - Popović, Aleksandar R.
AU  - Vrvić, Miroslav M.
AU  - Nikolić, Vladimir
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2300
AB  - Novel macromolecular graft copolymers were synthesized by reaction of the hydroxyl groups of the microbial polysaccharide levan, produced using Bacillus licheniformis, with polystyrene (Lev-g-PS). Synthesis was performed by the free radical reaction using potassium persulfate (PPS) as initiator. The prepared copolymer was characterized by FTIR, SEM, TG/DTA, XRD and C-13 NMR. The influence of the different conditions (reaction temperature, air or nitrogen atmosphere, reaction time, type of amines and ascorbic acid (AA) concentration) on the grafting reaction was investigated. Results showed that maximum percentage of grafting (58.1%) was achieved at a reaction temperature 70 degrees C, in a nitrogen atmosphere and using dimethylethanolamine (DMEA) as the amine activator. On the basis of the obtained results, the likely reaction mechanism was proposed. Synthesized copolymers have better thermal stability in comparison with their initial components. Copolymers such as Lev-g-PS could potentially have many applications, such as compatibilizers and material for membranes. (C) 2016 Elsevier Ltd. All rights reserved.
PB  - Elsevier Sci Ltd, Oxford
T2  - Carbohydrate Polymers
T1  - Synthesis and characterization of a new type of levan-graft-polystyrene copolymer
VL  - 154
SP  - 20
EP  - 29
DO  - 10.1016/j.carbpol.2016.08.001
UR  - Kon_3116
ER  - 
@article{
author = "Kekez, Branka and Gojgić-Cvijović, Gordana D. and Jakovljević, Dragica M. and Pavlović, Vladimir D. and Beškoski, Vladimir and Popović, Aleksandar R. and Vrvić, Miroslav M. and Nikolić, Vladimir",
year = "2016",
abstract = "Novel macromolecular graft copolymers were synthesized by reaction of the hydroxyl groups of the microbial polysaccharide levan, produced using Bacillus licheniformis, with polystyrene (Lev-g-PS). Synthesis was performed by the free radical reaction using potassium persulfate (PPS) as initiator. The prepared copolymer was characterized by FTIR, SEM, TG/DTA, XRD and C-13 NMR. The influence of the different conditions (reaction temperature, air or nitrogen atmosphere, reaction time, type of amines and ascorbic acid (AA) concentration) on the grafting reaction was investigated. Results showed that maximum percentage of grafting (58.1%) was achieved at a reaction temperature 70 degrees C, in a nitrogen atmosphere and using dimethylethanolamine (DMEA) as the amine activator. On the basis of the obtained results, the likely reaction mechanism was proposed. Synthesized copolymers have better thermal stability in comparison with their initial components. Copolymers such as Lev-g-PS could potentially have many applications, such as compatibilizers and material for membranes. (C) 2016 Elsevier Ltd. All rights reserved.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Carbohydrate Polymers",
title = "Synthesis and characterization of a new type of levan-graft-polystyrene copolymer",
volume = "154",
pages = "20-29",
doi = "10.1016/j.carbpol.2016.08.001",
url = "Kon_3116"
}
Kekez, B., Gojgić-Cvijović, G. D., Jakovljević, D. M., Pavlović, V. D., Beškoski, V., Popović, A. R., Vrvić, M. M.,& Nikolić, V.. (2016). Synthesis and characterization of a new type of levan-graft-polystyrene copolymer. in Carbohydrate Polymers
Elsevier Sci Ltd, Oxford., 154, 20-29.
https://doi.org/10.1016/j.carbpol.2016.08.001
Kon_3116
Kekez B, Gojgić-Cvijović GD, Jakovljević DM, Pavlović VD, Beškoski V, Popović AR, Vrvić MM, Nikolić V. Synthesis and characterization of a new type of levan-graft-polystyrene copolymer. in Carbohydrate Polymers. 2016;154:20-29.
doi:10.1016/j.carbpol.2016.08.001
Kon_3116 .
Kekez, Branka, Gojgić-Cvijović, Gordana D., Jakovljević, Dragica M., Pavlović, Vladimir D., Beškoski, Vladimir, Popović, Aleksandar R., Vrvić, Miroslav M., Nikolić, Vladimir, "Synthesis and characterization of a new type of levan-graft-polystyrene copolymer" in Carbohydrate Polymers, 154 (2016):20-29,
https://doi.org/10.1016/j.carbpol.2016.08.001 .,
Kon_3116 .
15
14
14

Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9

Krstić, Natalija M.; Pavlović, Vladimir D.; Novaković, Irena T.; Matić, Ivana Z.; Sladić, Dušan

(Springer, Dordrecht, 2013)

TY  - DATA
AU  - Krstić, Natalija M.
AU  - Pavlović, Vladimir D.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3537
PB  - Springer, Dordrecht
T2  - Molecular Diversity
T1  - Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9
ER  - 
@misc{
author = "Krstić, Natalija M. and Pavlović, Vladimir D. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan",
year = "2013",
publisher = "Springer, Dordrecht",
journal = "Molecular Diversity",
title = "Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9"
}
Krstić, N. M., Pavlović, V. D., Novaković, I. T., Matić, I. Z.,& Sladić, D.. (2013). Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9. in Molecular Diversity
Springer, Dordrecht..
Krstić NM, Pavlović VD, Novaković IT, Matić IZ, Sladić D. Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9. in Molecular Diversity. 2013;..
Krstić, Natalija M., Pavlović, Vladimir D., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, "Supplementary data for article: Krstić, N. M.; Pavlović, V. D.; Novaković, I. T.; Matić, I. Z.; Sladić, D. Synthesis, Characterization and Biological Evaluation of Some Novel P-Heterocyclic Androst-4-Ene Derivatives. Molecular Diversity 2013, 17 (3), 547–561. https://doi.org/10.1007/s11030-013-9455-9" in Molecular Diversity (2013).

Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives

Krstić, Natalija M.; Pavlović, Vladimir D.; Novaković, Irena T.; Matić, Ivana Z.; Sladić, Dušan

(Springer, Dordrecht, 2013)

TY  - JOUR
AU  - Krstić, Natalija M.
AU  - Pavlović, Vladimir D.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1376
AB  - The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.
PB  - Springer, Dordrecht
T2  - Molecular Diversity
T1  - Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives
VL  - 17
IS  - 3
SP  - 547
EP  - 561
DO  - 10.1007/s11030-013-9455-9
UR  - Kon_2496
ER  - 
@article{
author = "Krstić, Natalija M. and Pavlović, Vladimir D. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan",
year = "2013",
abstract = "The reactions of 21-hydroxyprogesterone with Lawesson's reagent in toluene or gave four P-heterocyclic androst-4-ene derivatives (two tautomeric pairs): 4-(3-thioxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2- sulfide (2), 4-(3-thioxoandrost-4-en-17-ylidene)-1,3,2-oxathiaphospholane-2-sulfide (3), 4-(3-oxoandrost-4-en-17-yl)-1,3,2-oxathiaphosphole-2-sulfide (4), and 4-(3-oxoandrost-4-en-17-ylidene)-1,3,2- oxathiaphospholane-2-sulfide (5). The structures of all novel 17-substituted steroids were elucidated from their analytic and spectral data (HRMS, IR, 1D NMR and 2D NMR-HSQC, HMBC, NOESY, COSY). The detailed NMR analysis for all compounds revealed the presence of two pairs of signals in approx. 8:2 ratio indicating the existence of two diastereoisomers (a and b) with different configurations at the phosphorus atom. A parallel analysis of heteronuclear 2D - spectra (HSQC and HMBC) and homonuclear 2D spectra (NOESY and COSY) enabled complete and assignments of each isomer and provided evidence for the preferred configuration on phosphorus atom. Cytotoxic activity in vitro was tested against four tumor cell lines (human cervix carcinoma HeLa cells, chronic myelogenous leukemia K-562 and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compounds 3a,b and 4a,b showed a poor activity against HeLa and MDA-MB-453 cell lines, while against MDA-MB-361 cell line, all tested compounds exerted very weak cytotoxic effect. All compounds exerted moderate activity against K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina were evaluated. All tested compounds showed strong antifungal activity.",
publisher = "Springer, Dordrecht",
journal = "Molecular Diversity",
title = "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives",
volume = "17",
number = "3",
pages = "547-561",
doi = "10.1007/s11030-013-9455-9",
url = "Kon_2496"
}
Krstić, N. M., Pavlović, V. D., Novaković, I. T., Matić, I. Z.,& Sladić, D.. (2013). Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity
Springer, Dordrecht., 17(3), 547-561.
https://doi.org/10.1007/s11030-013-9455-9
Kon_2496
Krstić NM, Pavlović VD, Novaković IT, Matić IZ, Sladić D. Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives. in Molecular Diversity. 2013;17(3):547-561.
doi:10.1007/s11030-013-9455-9
Kon_2496 .
Krstić, Natalija M., Pavlović, Vladimir D., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, "Synthesis, characterization and biological evaluation of some novel P-heterocyclic androst-4-ene derivatives" in Molecular Diversity, 17, no. 3 (2013):547-561,
https://doi.org/10.1007/s11030-013-9455-9 .,
Kon_2496 .
7
7
7

New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities

Krstić, Natalija M.; Bjelaković, Mira S.; Pavlović, Vladimir D.; Robeyns, Koen; Juranić, Zorica D.; Matić, Ivana Z.; Novaković, Irena T.; Sladić, Dušan

(Elsevier Science Inc, New York, 2012)

TY  - JOUR
AU  - Krstić, Natalija M.
AU  - Bjelaković, Mira S.
AU  - Pavlović, Vladimir D.
AU  - Robeyns, Koen
AU  - Juranić, Zorica D.
AU  - Matić, Ivana Z.
AU  - Novaković, Irena T.
AU  - Sladić, Dušan
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1282
AB  - The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
VL  - 77
IS  - 5
SP  - 558
EP  - 565
DO  - 10.1016/j.steroids.2012.01.021
UR  - Kon_2305
ER  - 
@article{
author = "Krstić, Natalija M. and Bjelaković, Mira S. and Pavlović, Vladimir D. and Robeyns, Koen and Juranić, Zorica D. and Matić, Ivana Z. and Novaković, Irena T. and Sladić, Dušan",
year = "2012",
abstract = "The reactions of 17 alpha-hydroxyprogesterone with Lawesson's reagent (LR) in toluene, CH2Cl2 and/or CCl4 gave, depending on the duration of the reaction, two diastereoisomeric androst-4-en-17-spiro-1,3,2-oxathiaphospholane-2-sulfide pairs 2a,b and 3a,b in approximately 7:3 ratio, differing in configuration at the phosphorus atom. A parallel analysis of heteronuclear 2D H-1-C-13 spectra (HSQC and HMBC) and homo-nuclear 2D spectra (NOESY) enabled complete H-1 and C-13 assignments of each isomer. Also, analysis of NOESY correlations provided evidence for the preferred conformation. X-ray analysis of 3a confirmed the structure and absolute configuration on phosphorus. A pathway for the formation of 1,3,2-oxathiaphospholane ring was proposed. Cytotoxic activity in vitro was tested against three tumor cell lines (human cervix carcinoma HeLa cells and two human breast carcinoma MDA-MB-361 and MDA-MB-453 cells). Compound 3a and mixture 3a,b showed a moderate activity against HeLa and MDA-MB-453 cell lines while against MDA-MB-361 cell line all tested compounds exerted very weak cytotoxic effect. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, toxicity to brine shrimp Artemia sauna, were evaluated. All tested compounds showed strong antifungal activity. (C) 2012 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities",
volume = "77",
number = "5",
pages = "558-565",
doi = "10.1016/j.steroids.2012.01.021",
url = "Kon_2305"
}
Krstić, N. M., Bjelaković, M. S., Pavlović, V. D., Robeyns, K., Juranić, Z. D., Matić, I. Z., Novaković, I. T.,& Sladić, D.. (2012). New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids
Elsevier Science Inc, New York., 77(5), 558-565.
https://doi.org/10.1016/j.steroids.2012.01.021
Kon_2305
Krstić NM, Bjelaković MS, Pavlović VD, Robeyns K, Juranić ZD, Matić IZ, Novaković IT, Sladić D. New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities. in Steroids. 2012;77(5):558-565.
doi:10.1016/j.steroids.2012.01.021
Kon_2305 .
Krstić, Natalija M., Bjelaković, Mira S., Pavlović, Vladimir D., Robeyns, Koen, Juranić, Zorica D., Matić, Ivana Z., Novaković, Irena T., Sladić, Dušan, "New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities" in Steroids, 77, no. 5 (2012):558-565,
https://doi.org/10.1016/j.steroids.2012.01.021 .,
Kon_2305 .
22
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25

Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids

Bjelaković, Mira S.; Krstić, Natalija M.; Milić, Dragana; Kop, Tatjana; Robeyns, Koen; Pavlović, Vladimir D.

(Pergamon-Elsevier Science Ltd, Oxford, 2012)

TY  - JOUR
AU  - Bjelaković, Mira S.
AU  - Krstić, Natalija M.
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Robeyns, Koen
AU  - Pavlović, Vladimir D.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1329
AB  - The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed. (C) 2012 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids
VL  - 68
IS  - 36
SP  - 7479
EP  - 7488
DO  - 10.1016/j.tet.2012.06.024
UR  - Kon_2353
ER  - 
@article{
author = "Bjelaković, Mira S. and Krstić, Natalija M. and Milić, Dragana and Kop, Tatjana and Robeyns, Koen and Pavlović, Vladimir D.",
year = "2012",
abstract = "The present study is concerned with the oxidative behaviour of unsaturated and epoxy 5-oxo-5,10-secosteroids in the presence of m-CPBA or TFAA-UHP as oxidants in order to investigate potential parameters controlling the chemoselectivity and regioselectivity. In the study we discovered a striking difference in the chemical behaviour of stereoisomeric compounds, (Z)- and (E)-3 beta-acetoxy-5,10-secocholest-1(10)-en-5-ones, as well as 1S,10R- and 1R,10R-epoxides. The secoketones were oxidized with exclusively C-6 migration and Baeyer-Villiger rearrangement product formation, whereas their stereoisomers provided the ring-contracted products, without lactone formation. The preferred conformation of expanded and contracted rings was established by NOESY correlations. The structures of two obtained lactones were also confirmed by X-ray analysis. The mechanistic and stereochemical aspects of these transformations are discussed. (C) 2012 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids",
volume = "68",
number = "36",
pages = "7479-7488",
doi = "10.1016/j.tet.2012.06.024",
url = "Kon_2353"
}
Bjelaković, M. S., Krstić, N. M., Milić, D., Kop, T., Robeyns, K.,& Pavlović, V. D.. (2012). Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 68(36), 7479-7488.
https://doi.org/10.1016/j.tet.2012.06.024
Kon_2353
Bjelaković MS, Krstić NM, Milić D, Kop T, Robeyns K, Pavlović VD. Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids. in Tetrahedron. 2012;68(36):7479-7488.
doi:10.1016/j.tet.2012.06.024
Kon_2353 .
Bjelaković, Mira S., Krstić, Natalija M., Milić, Dragana, Kop, Tatjana, Robeyns, Koen, Pavlović, Vladimir D., "Oxidative 10-membered ring expansion and contraction of stereoisomeric 1(10)-unsaturated and 1,10-epoxy-5-oxo-5,10-secosteroids induced by peracids" in Tetrahedron, 68, no. 36 (2012):7479-7488,
https://doi.org/10.1016/j.tet.2012.06.024 .,
Kon_2353 .
1
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2